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Electronic contributor forms are actually on the PSF wishlist. We'll get there some day (maybe after the website update).
Getting back to the problem at hand, I think you might be on to something with the idea of exploiting PEP 409 to handle this. Specifically, where we reraise a caught exception when there are no exception details active, we should be able to replace the bare raise with something like:
 # A containing with statement will automatically add the exception
 # context back in after it gets suppressed. Avoid displaying it.
 if suppressed_exc and exc_details == (None, None, None):
 raise exc from None
 raise
That way, the exception *display* of escaping exceptions will still match that of nested with statements, even though the attributes are subtly different (__suppress_context__ being set to True, rather than __context__ being None)